Journal of Natural Products 最新文献_第3页

Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-04 DOI: 10.1021/acs.jnatprod.4c01247

Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe

{"title":"Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam.","authors":"Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe","doi":"10.1021/acs.jnatprod.4c01247","DOIUrl":"10.1021/acs.jnatprod.4c01247","url":null,"abstract":"The tropical plant Aglaia perviridis is known to produce cyclopenta[b]benzofuran and other types of rocaglate derivatives including silvestrol (3) and 5‴-episilvestrol (4) that are of current pharmacological interest. In the present work, further investigation of A. perviridis roots collected in Vietnam has yielded two new rocaglate acetonide derivatives (1 and 2) and a known pentanor-3,4-seco-dammarane triterpenoid (7) found for the first time as a natural product, in addition to four known rocaglates (3-6). The structures of compounds 1 and 2 were confirmed by partial synthesis experiments, and their potential occurrence as extraction artifacts was investigated by targeted selective ion monitoring using UHPLC-MS. All compounds obtained were evaluated against a panel of four human cancer cell lines, in which the six rocaglate derivatives (1-6) tested all showed submicromolar potencies.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"662-670"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11960728/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555348","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ohauamines A-D, Structurally Unprecedented Tricyclic Depsi-tripeptides from the New Zealand Ascidian Pycnoclavella kottae.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-20 DOI: 10.1021/acs.jnatprod.5c00033

Dan Chen, Florent Rouvier, Robert Keyzers, Marie-Lise Bourguet-Kondracki, Jean Michel Brunel, Melissa M Cadelis, Brent R Copp

引用次数: 0

Seven New Guanidine Derivatives and One New Hypoxanthine Derivative Isolated from the Scorpion Buthus martensii and Potential Anti-Neuroinflammatory Activity.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-03 DOI: 10.1021/acs.jnatprod.5c00040

Ke-Ming Li, Wei-Fen Li, Yong-Ming Yan, Guangyi Yang, Yong-Xian Cheng

引用次数: 0

Analgesic Grayanane-Derived Diterpenoids from the Flowers of Rhododendron molle.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-11 DOI: 10.1021/acs.jnatprod.4c01303

Yang Song, Hui-Min Yan, Bing Chai, Zhao-Xin Zhang, Fang-Fei Li, Qin-Yan Shi, Hai-Qiang Wang, Yong Li, Shi-Shan Yu

引用次数: 0

Alstolarsines A-E, Indoline Alkaloids with Two Different Carbon Skeletons from Alstonia scholaris.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-14 DOI: 10.1021/acs.jnatprod.5c00027

Xu-Xin Zhu, Yao-Yue Fan, Cheng-Yu Zheng, Hong-Ying Yang, Kun Gao, Jian-Min Yue

引用次数: 0

Development of a Proton Spin Network Fingerprint Library to Support Mass Spectrometry-Based Identification of Pharmacophore-Bearing Constituents in the Botanical Supplement Centella asiatica.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 DOI: 10.1021/acs.jnatprod.4c01486

Sara Neiheisel, Dmitriy Uchenik, Luke Marney, Claudia S Maier, Nora E Gray, Amala Soumyanath, Harinantenaina L Rakotondraibe

{"title":"Development of a Proton Spin Network Fingerprint Library to Support Mass Spectrometry-Based Identification of Pharmacophore-Bearing Constituents in the Botanical Supplement Centella asiatica.","authors":"Sara Neiheisel, Dmitriy Uchenik, Luke Marney, Claudia S Maier, Nora E Gray, Amala Soumyanath, Harinantenaina L Rakotondraibe","doi":"10.1021/acs.jnatprod.4c01486","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01486","url":null,"abstract":"Centella asiatica (L.) Urban (Apiaceae) has been utilized for centuries in traditional medicine systems in Southeast Asia and Southern Africa, including Madagascar. Previous studies have reported evidence of the therapeutic potential of C. asiatica formulations in models of Alzheimer's Disease and other dementias. Caffeoylquinic acids (CQAs) have been identified to be among the pharmacologically relevant metabolites contributing to the botanical's cognitive enhancement and neuroprotective effects. Isomers of CQAs are, however, difficult to differentiate by commonly used LC-MS techniques, making the characterization, standardization, and batch-to-batch consistency of these formulations challenging. Individual CQAs have unique proton Spin Network Fingerprints (pSNFs) that can be used to distinguish between CQA regioisomers within complex extracts. This work describes the development of a CQA-focused pSNF library that can be used to complement LC-MS methods for the accurate metabolite identification and characterization of bioactive C. asiatica fractions and extracts. The isolation of two new (1 and 2) and four known (3-6) CQAs and CQA analogues from C. asiatica and their contribution to the pSNF library are also discussed herein.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143727090","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Xiapyrroles A-F: N-Alkylpyrrole Alkaloids from the Marine-Derived Actinomycete Streptomyces xiamenensis 1310KO-148.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-19 DOI: 10.1021/acs.jnatprod.4c01491

Min Ah Lee, Jong Soon Kang, Yeo Dae Yoon, Hwa-Sun Lee, Chang-Su Heo, Sun Joo Park, Hee Jae Shin

{"title":"Xiapyrroles A-F: N-Alkylpyrrole Alkaloids from the Marine-Derived Actinomycete Streptomyces xiamenensis 1310KO-148.","authors":"Min Ah Lee, Jong Soon Kang, Yeo Dae Yoon, Hwa-Sun Lee, Chang-Su Heo, Sun Joo Park, Hee Jae Shin","doi":"10.1021/acs.jnatprod.4c01491","DOIUrl":"10.1021/acs.jnatprod.4c01491","url":null,"abstract":"Six new N-alkylpyrrole alkaloids (1-6) were isolated from the marine-derived actinomycete Streptomyces xiamenensis 1310KO-148 from a sponge sample. The structures of xiapyrroles A-F (1-6) were elucidated by detailed analysis of extensive spectroscopic data, including 1D, 2D NMR, and HRESIMS data. The absolute configurations of 2, 3, 4, and 6 were determined by a comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. The position of the hydroxamate group in 6 was confirmed through NO-methylation and NOESY data analysis. All compounds (1-6) were tested for their anti-inflammatory effects in LPS-stimulated RAW 264.7 cells, a mouse macrophage cell line. The treatment of RAW 264.7 cells with 30 μM of 1-6 showed no significant cytotoxic effects. However, 1 dose-dependently suppressed the LPS-induced production of NO (IC50 = 29.5 μM) and interleukin-6 (IL-6) (IC50 = 10.9 μM). Compound 1 exhibited no potential cytotoxicity against six solid cancer cell lines and eight blood cancer cell lines at a concentration of 30 μM.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"797-805"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661672","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Structure and Synthesis of Amatyemides A and B, Cyclic Octadepsipeptides from South African Stromatolites.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-16 DOI: 10.1021/acs.jnatprod.4c01446

George F Neuhaus, Xinhui Yu, Wakana Osaka, Rikito Suzuki, Daphne R Mattos, Julius C Habiyaremye, Kyle K Axt, Sophia E Bonar, Alexandros Polyzois, Rosemary A Dorrington, Jane E Ishmael, Shinya Oishi, Kerry L McPhail

{"title":"Structure and Synthesis of Amatyemides A and B, Cyclic Octadepsipeptides from South African Stromatolites.","authors":"George F Neuhaus, Xinhui Yu, Wakana Osaka, Rikito Suzuki, Daphne R Mattos, Julius C Habiyaremye, Kyle K Axt, Sophia E Bonar, Alexandros Polyzois, Rosemary A Dorrington, Jane E Ishmael, Shinya Oishi, Kerry L McPhail","doi":"10.1021/acs.jnatprod.4c01446","DOIUrl":"10.1021/acs.jnatprod.4c01446","url":null,"abstract":"An investigation of living phosphatic stromatolites from Schoenmakerskop barrage pool near Gqeberha (Port Elizabeth), South Africa, yielded new cyclic octadepsipeptides, amatyemides A (1) and B (2), named using the Xhosa word 'amatye' for 'rock'. The amatyemides were isolated from methanol extracts of a targeted stromatolite sample collection, following an initial metabolomic survey of the Schoenmakerskop pool. Planar structure elucidation of 1 and 2 relied on NMR and LCMS2 data, which delineated the same six amino acids and one 2-hydroxy-3-methylpentanoic acid (Hmpa) residues in each compound. The two octadepsipeptides differed only in the presence of a 2-hydroxydodecanoic acid (Hdda) residue in 1 and a 2-hydroxydecanoic acid (Hda) residue in 2. The absolute configurations of most amino acid residues in 1 were determined using an enhanced Marfey's reagent. The configurations of the 2-hydroxy acids and O-methylthreonine were assigned, and the absolute structures of amatyemides A (1) and B (2) were confirmed, by total solid-phase peptide synthesis of two possible diastereomers for each natural product. Biological testing of natural and synthetic amatyemides against human U87-MG glioblastoma, HCT116 colon, and SH-SY5Y neuroblastoma cells revealed weak, cell-type specific, cytotoxic potential where 2 > 1, and this was attributed to induction of oxidative stress by 2.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"747-756"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143646525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ingenane Diterpenoids from Euphorbia peplus as Potential New CHK1 Inhibitors That Sensitize Cancer Cells to Chemotherapy.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-08 DOI: 10.1021/acs.jnatprod.4c01343

Mi Zhou, Yanlan Yang, Shoulun He, Qiannan Xu, Chunchun Du, Wenjing Tian, Haifeng Chen

{"title":"Ingenane Diterpenoids from Euphorbia peplus as Potential New CHK1 Inhibitors That Sensitize Cancer Cells to Chemotherapy.","authors":"Mi Zhou, Yanlan Yang, Shoulun He, Qiannan Xu, Chunchun Du, Wenjing Tian, Haifeng Chen","doi":"10.1021/acs.jnatprod.4c01343","DOIUrl":"10.1021/acs.jnatprod.4c01343","url":null,"abstract":"Phosphorylation of checkpoint kinase 1 at Ser-345 (p-CHK1(S345)) mediates the replication stress response in cancer cells, leading to chemotherapy resistance. Therefore, finding inhibitors of p-CHK1(S345) is currently a promising strategy to prevent acquired drug resistance. In this study, 14 ingenane diterpenoids (1-14), involving two undescribed compounds possessing an unprecedented exocyclic double bond Δ6(20), were identified from Euphorbia peplus. The inhibitory effects of the isolated compounds on p-CHK1(S345) and their structure-activity relationship (SAR) were investigated. Compounds 7 and 8 presented the strongest inhibitory effects, abrogated cell cycle arrest, and caused the accumulation of DNA damage, improving the sensitivity of cancer cells to chemotherapeutic drugs. An in vivo assay confirmed the enhancement of 8 on the anticancer effect of topotecan via blocking of p-CHK1(S345). Mechanistically, 8 increased CHK1 ubiquitination to inhibit p-CHK1(S345) via activation of protein kinase C (PKC). PKC activation was first found to enhance CHK1 ubiquitination to block p-CHK1(S345). Above all, this finding not only indicates that compound 8 could be developed as a novel CHK1 inhibitor but also reveals a previously unrecognized role of PKC in regulating cancer chemotherapy sensitivity.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"688-705"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143582140","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

LC-MS Guided Discovery and Biosynthetic Pathway of Coprisamides E-H, Cinnamic Acid-Containing Metabolites from the Marine Algae-Derived Streptomyces thermolineatus NAK03196.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-03 DOI: 10.1021/acs.jnatprod.4c01439

Guo Dong Zhang, Zhi Wei Yang, Fang Zhou Yin, Zhang Yuan Yan, Zi Jun Xiong, Shuai Ma, Zhi Kai Guo, Rui Hua Jiao

引用次数: 0